Odor inhibition for paraffin hydrocarbons

ABSTRACT

Odor formation is inhibited in paraffin hydrocarbon compositions with normal boiling points within the range of from about 70*F. to about 700*F. by the addition of a small amount of a bis(alkylhydroxybenzyl) ether.

United States Patent [191 Reusser ODOR INHIBITION FOR PARAFFINHYDROCARBONS [75] Inventor: Robert E. Reusser, Bartiesville,

Okla.

[73] Assignee: Phillips Petroleum Company,

Bartlesville, Okla.

[22] Filed: May 14, 1973 [2!] Appl. No.: 359,790

[52] US. Cl. 44/78; 252/52; 252/404 [5]] Int. Cl Clol 1/18 [58] Field ofSearch 44/78; 252/52, 404

[56] References Cited UNITED STATES PATENTS [451 Sept. 16, 1975 9/l960Filbey 44/78 X 2/1968 Longoria 252/404 X Primary Examiner-Delbert E.Gantz Assistant Eraminer-l. Vaughn [57] ABSTRACT 4 Claims, N0 DrawingsODOR INHIBITION FOR PARAFFIN.

HYrDROCARBONS BACKGROUND OF THE INVENTION I This inventionwelates toparaffin hydrocarbons. Inv one of its aspects, this invention relates toodor'fqrma tion in paraffin hydrocarbon compositions. in another of itsaspects this invention, relates to inhibition of odor formation inparaffin hydrocarbon compositions. in one of its concepts this inventionrelates to the inhibition of an odor formation in paraffin hy drocarboncom positions by the addition of bis( alkylhydi'o xybenzyl) ether to theparaffin hydrocarbon composition.

Odorless mineral spirits" which are generally marketed for use as paintthinner, insecticide carrier oil, charcoal lighter fluid, industrialcleaning compounds, and solvents are generally composed of a mixture ofparaffin hydrocarbons boiling within the range of from about 70F toabout 700F. Under shelf storage conditions which include temperatures ofup to 125F. or even higher, uninhibited odorless mineral spirits do nottend to remain odorless. It is, therefore, common practice to add anagent effective for inhibiting odor formation to commercial mixtures ofthese hydrocarbons. We have discovered that certain bis(alkylhydroxybenzyl) ethers added in small amounts to paraffinhydrocarbons will inhibit the formation of odor bodies.

lt is therefore an object of this invention to provide a paraffinhydrocarbon composition stabilized against odor formation. It is also anobject of this invention to provide a method for stabilizing paraffinhydrocarbon compositions against odor formation.

Other aspects, concepts and objects of this invention are apparent fromthe study of the disclosure and the appended claims.

SUMMARY OF THE INVENTION According to the invention, odor formation inparaffin hydrocarbon compositions is inhibited by the addition of atleast one bis(alkylhydroxybenzyl) ether.

In one of the embodiments of this invention an odor inhibitedcomposition of matter comprising at least one paraffin hydrocarbon andat least one bis(alkylhy droxybenzyl) ether is provided.

Materials that can be inhibited against odor formation by the process ofthis invention are paraffin hydrocarbon compositions having normalboiling points within the range of from about 70F. to about 700F.Although individual hydrocarbons boiling within this range can beinhibited by the process of this invention, the process of thisinvention will usually be applied to mixtures of hydrocarbons boilingwithin the given range. Paraffin hydrocarbons boiling within the rangeof from about 240 to about 345F. such as the hydrocarbon mixturesSoltrol* 50 and Soltrol* 100, marketed by Phillips Petroleum Company,have been found to be particularly well adapted to this method of odorinhibition.

*A registered trademark of Phillips Petroleum Company Thebis(alkylhydroxybenzyl) ethers that have been found suitable as odorinhibiting agents for paraffin hydrocarbon compositions are those havingthe structural formula:

'lthas been found that even a trace. of the odor-.

stabilizing bis(alkylhydroxybenzyl) ether compounds described abovesufficient to stabilize a paraffin hydrocarbon composition. Usuallypanamount in the! range of between about 0.005 and=0.50 weight percent isused. A more preferable amount is in the range of about 0101 to about0.20 weight percent based on the weight of the paraffin hydrocarboncomposition being odor stabilized. Larger amounts can be Used, ifdesired, but we'have not found the of-larger antounts neces- Since theodor-stabilizing bis(alkylhydroxybenzyl) ethers are soluble in paraffinhydrocarbons in amounts in the range stated above, special means forintroducing the bis(alkylhydroxybenzyl) ether into the hydrocarbons areunnecessary.

The cause of odor formation in paraffin hydrocarbons has been determinedto be the formation of oxidation products which develop upon storage ofthe hydrocarbons probably because of oxidation of the small amount ofunsaturated hydrocarbon impurities which are associated with theirproduction and not completely separable from the paraffin hydrocarbons.The example below is offered to show the effectiveness of abis(alkylhydroxybenzyl) ether in preventing oxidation and, therefore,odor formation in a mixture of paraffin hydrocarbons.

EXAMPLE pressure drop on the bomb at various time intervals. "Aregistered trademark of Phillips Petroleum Company for branchedchainparaffin hydrocarbons.

TABLE of Oxygen Consumed No. of Days A B The control (Soltrol* 50 alone)(B) had a strong oxidized hydrocarbon odor (ketone-like odor) while (A)the Soltrol* 50 with 0.05 weight percentbis(3,5-ditert-butyl-4-hydroxybenzyl) ether was water clear andodorless.

A registered trademark of Phillips Petroleum Company Reasonablevariation and modification are possible within the scope of theforegoing disclosure and the appended claims the essence of which isthat the addition of bis(alkylhydroxybenzyl) ether to paraffinhydrocarbons with normal boiling points within the range of from about701. to about 700F. will prevent the formation of odor bodies in thecomposition.

I claim:

i. An odor stabilized composition of matter consisting essentially of amajor proportion of at least one paraffin hydrocarbon having a normalboiling point within the range of from about 70F to about 700F, a minorproportion of oxidizable, unsaturated hydrocarbon impurities and anoxidation stabilizing amount of bis(3,5- di-tcrt-butyl-4-hydroxybenzyl)ether.

2. A composition of matter of claim I wherein thebis(3,S-di-tert-butyl-4-hydroxybenzyl) ether is present in an amount inthe range of about 0.005 to about 0.50 weight percent based on theweight of the paraffin hydrocarbons present.

3. A method for inhibiting odor formation in paraffin hydrocarboncompositions consisting essentially of a major proportion of at leastone paraffin hydrocarbon having a normal boiling point within the rangeof from about F to about 700F. and a minor portion of oxidizable,unsaturated hydrocarbon impurities, said method comprising stabilizingthe composition with an oxidation inhibiting amount ofbis(3,5-di-tert-butyl-4- hydroxybenzyl) ether.

4. A method of claim 3 wherein the bis(3,5-di-tertbutyl-4-hydroxybenzyl)ether is present in an amount in the range of about 0.005 to about 0.50weight percent based on the weight of the paraffin hydrocarbons present.

1. AN ODOR STABILIZED COMPOSITION OF MATTER CONSISTING DROCARBON OF AMAJOR PROPORTION OF AT LEAST ONE PARAFFIN HYDROCARBON HAVING A NORMALBOILING POINT WITHIN THE RANGE OF FROM ABOUT 70*F TO ABOUT 700*F, AMINOR PROPORTION OF OXIDIZABLE, UNSATURATED HYDROCARBON IMPURITIES ANDAN OXIDATION STABILIZING AMOUNT OFBIS(3,5-DI-TERT-BUTYL-4-HYDROXYBENXYL) ETHER.
 2. A composition of matterof claim 1 wherein the bis(3,5-di-tert-butyl-4-hydroxybenzyl) ether ispresent in an amount in the range of about 0.005 to about 0.50 weightpercent based on the weight of the paraffin hydrocarbons present.
 3. Amethod for inhibiting odor formation in paraffin hydrocarboncompositions consIsting essentially of a major proportion of at leastone paraffin hydrocarbon having a normal boiling point within the rangeof from about 70*F to about 700*F, and a minor portion of oxidizable,unsaturated hydrocarbon impurities, said method comprising stabilizingthe composition with an oxidation inhibiting amount ofbis(3,5-di-tert-butyl-4-hydroxybenzyl) ether.
 4. A method of claim 3wherein the bis(3,5-di-tert-butyl-4-hydroxybenzyl) ether is present inan amount in the range of about 0.005 to about 0.50 weight percent basedon the weight of the paraffin hydrocarbons present.